7 Lessons I’ve Learned In Two Years of Self-Employment

Two years ago this month, I walked into my principal's office at the high school I had taught at for three years to do my exit interview. It's basically the last step in the resigning process, so I had already gotten through about a month of the awkward stuff that happens long before the interview.

Even though literally nobody understood why I was leaving or thought it was a solid plan, there weren't any hard feelings (that I know of). I didn't quit my job for any other reason than I was really passionate about personal finance and had a dream of owning my own business.

When I decided that I wanted to quit my band director job to run M$M full-time, I simultaneously made the decision that I was going to be as helpful as I possibly could until my last day at the school.

That included giving my thoughts on who should replace me, and even actively trying to recruit people that I thought would be best for the job.

Then, there was telling the kids that I wouldn't be there anymore (which was by far the most difficult part – kids tend to take teachers moving on to different things really hard sometimes). That was one of the few times in my life that I got legitimately choked up while I was talking to a group.

By the time I got to the exit interview, it was a piece of cake. The principal basically said, “Congrats, you're chasing your dreams and that's really cool,” and that was it. I drove away from the band hall a few days later for the last time and completely changed careers.

Now two years later, I've been able to really reflect on what it took to get to this point (and appreciate that I actually made it this far haha).

Here are 7 things I've learned about self-employment and blogging full-time in my first two years:

1. There is no exact blueprint for business success

Most people describe leaving your job for self-employment as a leap of faith, but now I really look at it differently. There is no blind leap that magically ends by landing on success.

It's way more like purposely falling into the deep end of a pool and not knowing how to swim at all.

Even two years later, I'm still trying to figure out what works and what doesn't, how to sell, what to charge, etc.

There are definitely guidelines you can follow, but everyone's path in business is different. Your strengths really determine what you'll focus on (especially in a solopreneur model like my business).

2. Business is pretty cut and dry

When I was a teacher, things seemed really complicated most of the time. I was asked to do things because “that was just how it was done” (like going to meetings that had literally nothing to do with me).

If you pushed back on things like that, you got your wrist slapped by an administrator.

Business is inherently different, especially from the ownership side of things. It's about making money. In my case it's also about helping people feel better about money and entertaining people as well, but if I'm not making money I can't do those things.

That might seem soul-less to a lot of people, but for me, it seems really simple and cuts a lot of drama and wasted time out of the equation. If you are doing something and it's profitable and good for your customer, keep doing it. If it's not profitable, do something else until it's profitable.

I don't have to do things “just because”. I do things that I think will grow the business and my brand.

3. The money is never enough and won't make you happy

I could have sworn that when I was making $50,000 a year that $100,000 would make me happy. It's not like I was unhappy though; I just thought that more money would make me even happier.

Ha surprise! Doesn't work that way at all (I can feel the collective eye roll and the, “Yeah, I'd like to see for myself“….but I know I'm right on this and do hope you find out someday).

Once I was making $100,000, I wanted $150,000. It looks like I'll probably make around $200,000 this year, and now my goal is $500,000 next year. Once I hit $500,000, I'll want $1,000,000.

Then I'll want $2,000,000, and then $5,000,000 and so on and so on.

If you aren't a fan of the pursuit, you can go nuts chasing a moving target like that because you won't be fulfilled when you hit the next big number. Fortunately, I enjoy the game a lot and understand now that the money isn't what drives happiness.

Read also: Does a higher salary lead to happiness?

4. You have to admit what you suck at and embrace what you're great at

Confession: I suck at sales meetings and pitching services to clients. I went on several face to face sales meetings when I first started running my business full-time, and they never worked haha.

I'd dress nicely and practice my talking points, but it just never went the way I wanted it to. I was always so uncomfortable, and I'm sure that showed when I was talking to a potential marketing client.

Now I just don't really do them anymore. Most of the marketing work I've secured was fully via emails, which is where I communicate the most effectively (I do write for a living after all).

That doesn't mean I won't do one if I have to, but I'm going in as myself and will let my previous and current work do the talking for me.

I will say though – I'm a lot more confident now than I used to be because I've had some success. I can sit down with a client and basically say: “I built one of the biggest millennial personal finance blogs in the world in less than two years using Facebook ads.”  Boom.

Also, I don't technically need new clients because I have so many income streams. It makes it easier to negotiate because they need me, not the other way around.

5. Growth is slow but seems to happen fast

This sounds a little oximoron-ish, but anyone that has owned a business would probably agree. When you're in the grind trying to make more sales or get more clients – it seems like it takes forever.

Then you sit down and look at where your business is compared to a year or two years ago, and it feels like it happened so fast!

6. Relationships are key

The saying ,”It's not what you know, it's who you know,” is 100% true.

Most of the gigs that I've gotten on the marketing side of my business so far didn't come from making random phone calls or spamming business owners' inboxes.

They came from getting a strong referral from friends or people that I had done good work for. That's why you have to make sure that you always do your best work (the same goes for blogging – my readers tell other people about my site because they like the content).

The other part of the referral equation is to always do business with integrity and treat people right. I could overcharge someone for setting up their Facebook marketing, but I'll make four times as much money when I treat the client right and get referrals to their business-owning friends.

7. Nothing is free. Ever.

As a teacher, I did a lot of free work. It was expected that you volunteer to do certain tasks or stay later without extra compensation. It always bothered me, but that's just the way it was and it works for that industry.

In business, people don't do free stuff. Even if there isn't financial compensation for something, it better provide value that I can use to make more money later on.

I'll do something for free if you can hook me up with a journalist that will write a story about my site. See what I mean?

There's nothing wrong with being nice to other people and helping them out, but there should always be a value proposition involved.

Where is M$M going to go in the future?

Honestly, I'm not totally sure yet. I'm going to start working on my marketing course for bloggers this summer, and will also take some time off to recharge the batteries so I can keep grinding again. If you want to get in on the course, sign up for the waiting list below.

The marketing course will cover:

• How to use your existing blog or one you're going to start soon to get marketing clients
• Every aspect of setting up a profitable, sustainable marketing business from your laptop
• What to charge for your services
• How to build your blog alongside your marketing business
• Legal structures you should use and how to pay yourself as a business owner
• Facebook marketing, SEO, Google Adwords, email campaigns, web design, and more!

Drop your email in the area below and you'll get updates on the course and exclusive marketing tips and content from me:

Here's to another two years! 🙂

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Posted in: Inspiration

About Millennial Money Man

Bobby Hoyt is a former band director who paid off $40,000 of student loan debt in 18 months on his teaching salary and then left his job to run Millennial Money Man full-time. He helps other Millennials earn more through side hustles, save more through budgeting tools and apps, and pay off debt. He is a personal finance expert who has been seen on Forbes, Reuters, MarketWatch, CNBC, International Business Times, Business Insider, US News, Yahoo Finance, and many other personal finance and entrepreneurship media outlets.

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